Benzyl Alcohol → 2-Benzyl-1-methoxy-4-methylbenzene

HRID 916309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916309
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:10]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 77314-MethylanisoleHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 205490312-Benzyl-1-methoxy-4-methylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
167.5 °C

Versuchsvorschrift

A mixture of 4-methylanisole (200 g, 1.64 mol), benzyl alcohol (40.0 g, 0.37 mol) and p-toluenesulfonic acid monohydrate (8.0 g, 0.042 mol) was stirred at 160 to 175° C. for two hours while eliminating water generated by the reaction. After excess 4-methylanisole was distilled off under reduced pressure (inner temperature, 132° C./25 mmHg (3.3 kPa), the residue was dissolved in toluene (50 ml) and then the organic layer was successively washed with water (20 ml), 10% aqueous caustic soda (20 ml) and water (20 ml). After the washed organic layer was concentrated, the residue was distilled under reduced pressure to collect a component fractionated at boiling point of 120-138° C. at 0.7 mmHg (0.09 kPa) as a main fraction (52.75 g, 67.2%). The component was analyzed by NMR to identify 2.7:1 mixture of 2-benzyl-4-methylanisole and 3-benzyl-4-methylanisole.

Aufarbeitung

  1. customgenerated by the reaction
  2. distillationAfter excess 4-methylanisole was distilled off under reduced pressure (inner temperature, 132° C./25 mmHg (3.3 kPa)
  3. dissolutionthe residue was dissolved in toluene (50 ml)
  4. washthe organic layer was successively washed with water (20 ml), 10% aqueous caustic soda (20 ml) and water (20 ml)
  5. concentrationAfter the washed organic layer was concentrated
  6. distillationthe residue was distilled under reduced pressure
  7. customto collect a component
  8. addition2.7:1 mixture of 2-benzyl-4-methylanisole and 3-benzyl-4-methylanisole

Quellen und Nachweise

ORD-Eintrag
ord-e1593a35aec94f148dfe91d91a306aad
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268257B1

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